#Vanlife and the Road Trip are core elements of modern Adventurists, and it all started with a man named Horatio Nelson Jackson in 1903.

Horatio Nelson Jackson departed San Francisco on May 23rd, 1903 for what was to become America’s first ever road trip – and all because of a 50 dollar bet made just 5 days prior.  It was also the same year that the “Frontier” in America was considered closed.  Together, both events would dramatically alter the course of exploration and adventure for the next century.

In everyday life, the 31 year old Horatio was a successful Burlington, Vermont physician.  He was in San Francisco on vacation with his wife when, while sharing a few beers with some friendly strangers at the local University Club, he insisted that he had what it took to drive a car across the US.  Keep in mind that the cars of 1903 were little more than expensive playthings for hobbyists and hadn’t really been proven to be worthy of such a bet.  But, 2 days after the bet, Horatio finalized the purchase of his first car, a Winton that he dubbed The Vermont after his home state.  He then hired a partner/mechanic, Samuel Crocker, who was a successful bicycle racer to accompany him on his journey east.  After two more days of planning and preparation, the two began their unbelievable impromptu journey eastward towards New York City.  With them they brought little more than a couple of coats, some protective canvas suits, a couple of sleeping bags, some blankets, canteens, a water bag, an ax, a shovel, a telescope, some bicycle repair tools, a few spare parts, a block and tackle, extra cans gasoline and oil, a camera, a rifle, a shotgun, and a couple of pistols.

Horatio Nelson Jackson's Road Trip Route

Horatio Nelson Jackson’s Road Trip Route Across America

By all accounts, Horatio’s bet was one made in the innocence of drunken exuberance.  His enthusiasm was matched only by his underestimate of the effort needed to accomplish the journey.  But if there was one thing Horatio had, it was a steadfast commitment to the dream.

As soon as they left San Francisco though, trouble began to chase them down.  15 miles into the journey, they blew the first of what would be many, many tires.  Jackson and Crocker replaced it with the only spare they had, which by the way, happened to be the only right-sized spare tire they could find before they left.  After repairing the flat, they stopped again in Sacramento, CA to replace & upgrade their all too dim headlights and met some friendly cyclists who offered them road maps to the local area.  Jackson was unable to replenish the tire he blew but was however able to purchase some slightly used inner tubes.  Having resupplied the best they could, they struck back out onto the open road er, open range

Generally speaking, America in 1903 had no roads between cities, towns, or any other landmarks for that matter.  What there was however, was a loose patchwork of wagon and horse trails connecting the sparse fabric of humanity.  Making matters worse, these trails were generally considered informal and weren’t typically mapped with any sense of care or accuracy.  Keep in mind that most of what we knew about getting around the countryside at this time was oriented around the range of travel comfortable for your horse – which on average was only about 10-20 miles.  This physical limitation defined the spaces people occupied at the last turn of the century and made wandering beyond these informal limits rare and difficult.  What ‘roads’ did exist, were holdovers from the wagon train trading routes of the 1850’s, 60’s, and 70’s…  the “Old West” of cowboy and Indian lore.

Heeding the omens of a previously failed attempt to cross the continent just a couple years earlier by automobile pioneer Alexander Winton (original builder of Horatio’s Winton) by way of the deserts of Nevada and Utah, the two explorers took a more northerly route through the Sacramento Valley along the remnants of the original Oregon Trail.  But still, troubles continued to plague Horatio and Jackson.

The rough and tumble wagon trails which they followed, combined with the noisiness of their Winton, rendered them unable to tell when they would lose valuable items off the back of the car.  At first they lost their cookware, but while still in California, Jackson also lost his glasses.  Later, somewhere in Idaho, they lost Jackson’s coat which contained most of the traveler’s money.

Horatio's dog Bud and co-pilot mechanic

Horatio’s dog Bud and co-pilot mechanic

In addition to the effect the rough roads had on their possessions, it also took its toll on the Winton and their equipment.  In Oregon, their path would often require them to ford streams – some of which were quick and easy while others would require them to get out, affix the block and tackle and man-haul their trusty steed across the raging torrents.  Tires, somewhat expectedly, continued to blow out – forcing them at times to wind rope around the wheel so it could act as rudimentary tire…  but at least they could go on.  On June 6th however, the car finally suffered a severe mechanical issue forcing them to stop all forward progress near Burns, Oregon for several days.  No sooner than Jackson had finished the repair however, that they then suffered a gasoline leak which wasted all their available fuel.  Broke down again, Jackson rented a bicycle from a nearby rancher, rode the 25 miles back to town, suffered his own flat tire, and eventually returned with the fuel.  Once underway again, it was only 3 days later that they ran out of oil.  Jackson walked back to the town of Vale, Oregon to stock up on oil for this latest repair.

Their luck would soon begin to slowly turn when they purchased Bud, a Pit Bull they obtained from a rancher near Caldwell, Idaho.  Soon enough though, while traveling though the alkali flats of eastern Oregon and Idaho, they noticed that the harsh environment irritated Bud’s eyes.  At the next available stop they outfitted Bud with a pair of goggles which Bud wore without fuss for most of the rest of the journey.  Soon after, the trio with Bud sporting his fashionable goggles, began to accumulate some fame along their journey.


Press Clipping from Horatio Nelson Jackson’s road trip across America

The further they pushed on through Idaho and Wyoming,  the more it seemed that the team would actually make it.  This growing glimmer of hope eventually attracted the attention of the Press, who would anticipate their next town arrival and show up to document their adventures.  At Mountain Home, Idaho they veered from the Oregon Trail for the first time since near the California border and turned south glancing by the southern edge of the Sawtooth Mountains.  At Hailey, Idaho, Crocker wired the Winton Motor Carriage Company for more parts, which, combined with the increasing press coverage, spurred the Winton car company to step up their support efforts since to them it meant an increased positive image of the company.   In Cheyenne, Wyoming, the trio took a short break as they waited for more money to come through the wire, and repaired yet another mechanical failure, this time to the wheel bearings.

After Cheyenne, Jackson and Horatio both knew that the hard part of the journey was now behind them.  But relief would not comfort them since they soon heard that competing corporate sponsored teams from both Packard and Oldsmobile were chasing them down hoping to steal the crown of “first across the US in a motor car.”   Packard had secretly been planning their journey for months before Horatio’s fateful 50 dollar bet, and Oldsmobile had hoped to show the world what assembly line manufactured cars were capable of.  The threat of the other teams would spur Jackson and Horatio on, pushing them to step up their pace across the unending Great Plains of Nebraska and beyond.

When the travelers reached Omaha, Nebraska on July 12 they were able to stitch together a few paved roads in between the stretches of older wagon trails.  Subsequently, their mileage took a sharp increase and their rate of trail damage sharply decreased.  They would finally begin to make up much needed time after so many days spent waiting for parts, repairs and money back in the Rocky Mountain high country.


Horatio, Jackson and Bud Passing through town

They arrived in New York City to a heroes welcome on July 26th, 1903 – sixty-three days, twelve hours and thirty minutes after leaving San Francisco.

Both Packard and Oldsmobile were unable to maintain their forward progress through the tough times of the Rockies and within a month each, they eventually gave up their efforts to beat Horatio, Jackson and Bud to be the first to complete a journey across the North American continent in an automobile.

Later life

Horatio eventually settled in Burlington, Vermont, with his wife Bertha and faithful co-pilot Bud. When World War I broke out, Jackson was considered too old to serve, but he contacted President Theodore Roosevelt and volunteered to became a commissioned officer.  Following the war, he became one of the founders of the American Legion, and twice ran for Governor of Vermont.  He owned a newspaper, a bank and radio station WCAX (now WVMT).